Month: November 2022

Prasanna, Gutta Lakshmi published the artcileSynthesis and antibacterial activity of benzothiazole analogues, Safety of 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Journal of Applicable Chemistry (Lumami, India) (2018), 7(6), 1558-1564, database is CAplus.

A series of novel benzothiazole fused derivatives I [R = Me, Cl, Br, I; R¹ = Me, OMe] was designed, synthesized and screened for their antibacterial activity against Escherichia coli (MTCC 40) (Gram-neg.) and Staphylococcus aureus (MTCC 96)(Gram-pos.) bacteria. Among them, derivative I [R = Cl; R¹ = Me] showed highest antibacterial activity against Gram-pos. and Gram-neg. bacteria.

Journal of Applicable Chemistry (Lumami, India) published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C14H12N2S, Safety of 2-(4-Aminophenyl)-6-methylbenzothiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Sharma, Neetesh Kumar published the artcileSynthesis and biological evaluation of 1-(6-chlorobenzo[d]thiazol-2-yl)-2-(disubstituted methylene)hydrazine derivatives, Name: 6-Chlorobenzothiazol-2-ylamine, the publication is Journal of Drug Delivery and Therapeutics (2019), 9(4-ASuppl.2), 561-572, database is CAplus.

Synthesis of a series of various 1-(6-chlorobenzo[d]thiazol-2-yl)-2-(disubstituted methylene)hydrazine derivatives (E/Z)-I [R¹ = Ph, Me; R² = Ph, Me, Et; R¹R² = -(CH₂)₅-], (E)-2-(6-chlorobenzo[d]thiazol-2-yl)-1-(7,7-dimethylbicyclo [2.2.1] heptan-2-ylidene) hydrazine and intermediates 6-chloro-2-amine-1,3-benzothiazole and 2-hydrazino-6-chloro-1,3-benzothiazole have been done. After spectral anal., antibacterial activity has been screened against S. aureus and E. coli.

Journal of Drug Delivery and Therapeutics published new progress about 95-24-9. 95-24-9 belongs to thiazole, auxiliary class Organic Pigment, name is 6-Chlorobenzothiazol-2-ylamine, and the molecular formula is C8H10S, Name: 6-Chlorobenzothiazol-2-ylamine.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Wells, Geoffrey published the artcile4-Substituted 4-Hydroxycyclohexa-2,5-dien-1-ones with Selective Activities against Colon and Renal Cancer Cell Lines, COA of Formula: C14H12N2S, the publication is Journal of Medicinal Chemistry (2003), 46(4), 532-541, database is CAplus and MEDLINE.

The synthesis and antitumor evaluation of a series of new heteroaromatic- and aromatic-substituted hydroxycyclohexadienones (quinols), and their imine counterparts, are described. The quinols were synthesized via the addition of a lithiated aromatic moiety to a quinone ketal followed by deprotection. When the aromatic portion of the mol. is a fused heterobicyclic structure (e.g., benzothiazole derivative I), potent in vitro antitumor activity was observed in HCT 116 (GI₅₀ = 40 nM) and HT 29 (GI₅₀ = 380 nM) human colon as well in as MCF-7 and MDA 468 human breast cancer cell lines. When examined on the NCI Developmental Therapeutics Screening Program in vitro screen (60 human cancer cell lines), active compounds in this series consistently displayed a highly unusual pattern of selectivity; cytotoxicity (LC₅₀) was concentrated in certain colon and renal cell lines only. I also showed in vivo antitumor activity against human RXF 944XL renal xenografts in nude NMRI mice and is the focus of further study.

Journal of Medicinal Chemistry published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C18H26ClN3O, COA of Formula: C14H12N2S.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Karlsson, H. Jonas published the artcileSyntheses and DNA-binding studies of a series of unsymmetrical cyanine dyes: structural influence on the degree of minor groove binding to natural DNA, Application of 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Bioorganic & Medicinal Chemistry (2004), 12(9), 2369-2384, database is CAplus and MEDLINE.

Twelve crescent-shaped unsym. dyes have been synthesized and their interactions with DNA have been investigated by spectroscopic methods. A new facile synthetic route to this type of cyanine dyes has been developed, involving the preparation of 6-substituted 2-thiomethyl-benzothiazoles in good yields. The new dyes are analogs to the minor groove binding unsym. cyanine dye, BEBO, recently reported by us. In this dye, the structure of the known intercalating cyanine dye BO was extended with a 6-methylbenzothiazole substituent. Herein we further investigate the role of the extending benzazole heterocycle, as well as of the pyridine or quinoline moiety of the cyanine chromophore, for the binding mode of these crescent-shaped dyes to calf thymus DNA. Flow LD and CD studies of the 12 dyes show that the extent of minor groove binding to mixed sequence DNA varies significantly between the dyes. We find that hydrophobicity and size are the crucial parameters for recognition of the minor groove. The relatively high fluorescence quantum yield of many of these cyanines bound to DNA, combined with their absorption at long wavelengths, may render them useful in biol. applications. In particular, two of the benzoxazole containing dyes BOXTO and 2-BOXTO show a high degree of minor groove binding and quantum yields of 0.52 and 0.32, resp., when bound to DNA.

Bioorganic & Medicinal Chemistry published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C14H12N2S, Application of 2-(4-Aminophenyl)-6-methylbenzothiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Ukrainets, I. V. published the artcileSynthesis, spectral characteristics and biological properties of 1-furfuryl-4-hydroxy-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxylic acid anilides and heterylamides, Application In Synthesis of 92-36-4, the publication is Zhurnal Organichnoi ta Farmatsevtichnoi Khimii (2007), 5(1), 32-38, database is CAplus.

With the purpose of determination of regularities of their structure-antituberculosis activity relationship, the synthesis of 1-furfuryl-4-hydroxy-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxylic acids N-R-amides has been carried out. The peculiarities of the NMR spectra of the compounds synthesized and the results of studying of their antimycobacterial activity are discussed.

Zhurnal Organichnoi ta Farmatsevtichnoi Khimii published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C39H35N5O8, Application In Synthesis of 92-36-4.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Haj-Yehia, Abdullah I. published the artcileDetermination of aliphatic thiols by fluorometric high-performance liquid chromatography after precolumn derivatization with 2-(4-N-maleimidophenyl)-6-methylbenzothiazole, Safety of 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Pharmaceutical Research (1995), 12(1), 155-60, database is CAplus and MEDLINE.

A sensitive, fluorometric high-performance liquid chromatog. method for the detection of aliphatic thiols, following pre-column derivatization with 2-(4-N-maleimidophenyl)-6-methylbenzothiazole, has been developed. The N-maleimide, the acid and the Me ester derivatives of the com. available 2-(4-aminophenyl)-6-methylbenzothiazole were synthesized and found to be equally effective for the precolumn derivatization procedure. The resulting fluorescent derivatives of aliphatic thiols were separated on a reversed-phase column (Ultrasphere-ODS) using 0.1% hexane-sulfonic acid in 10 mM potassium hydrogen phosphate:acetonitrile (65:35) as a mobile phase and were detected fluorometrically (excitation 320 nm; emission 405 nm). The method is highly sensitive (femtomole range) and is easily applied for determination of SH-containing drugs and endogenous thiols in biol. samples.

Pharmaceutical Research published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C14H12N2S, Safety of 2-(4-Aminophenyl)-6-methylbenzothiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Schmidt, Monika published the artcileBenzothiazolyl ureas are low micromolar and uncompetitive inhibitors of 17β-HSD10 with implications to Alzheimer’s disease treatment, Quality Control of 95-24-9, the publication is International Journal of Molecular Sciences (2020), 21(6), 2059, database is CAplus and MEDLINE.

Human 17β-hydroxysteroid dehydrogenase type 10 is a multifunctional protein involved in many enzymic and structural processes within mitochondria. This enzyme was suggested to be involved in several neurol. diseases, e.g., mental retardation, Parkinson’s disease, or Alzheimer’s disease, in which it was shown to interact with the amyloid-beta peptide. We prepared approx. 60 new compounds based on a benzothiazolyl scaffold and evaluated their inhibitory ability and mechanism of action. The most potent inhibitors contained 3-chloro and 4-hydroxy substitution on the Ph ring moiety, a small substituent at position 6 on the benzothiazole moiety, and the two moieties were connected via a urea linker (4at, 4bb, and 4bg). These compounds exhibited IC₅₀ values of 1-2μ and showed an uncompetitive mechanism of action with respect to the substrate, acetoacetyl-CoA. These uncompetitive benzothiazolyl inhibitors of 17β-hydroxysteroid dehydrogenase type 10 are promising compounds for potential drugs for neurodegenerative diseases that warrant further research and development.

International Journal of Molecular Sciences published new progress about 95-24-9. 95-24-9 belongs to thiazole, auxiliary class Organic Pigment, name is 6-Chlorobenzothiazol-2-ylamine, and the molecular formula is C7H5ClN2S, Quality Control of 95-24-9.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Chelalba, Imane published the artcilePhytochemical composition and biological activity of Neurada procumbens L. growing in southern Algeria, Category: thiazole, the publication is Journal of Food Processing and Preservation (2020), 44(10), e14774, database is CAplus.

Neurada procumbens L. (Neuradaceae) is one of the most popular plants in the province of El-Oued in south-eastern Algeria. This study aimed to determine the antioxidant effectiveness of the 80% methanol extract of the aerial parts of the plant via the study of three-way antioxidant activity namely, 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), Catalase activity (CAT), and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging capacity assays in addition to examining its inhibitory capacity on the proliferation of hepatic (HepG2) and colon cancer (HCT116) cells. Chem. profiling of the major constituents of its extract was tentatively done using LC-MS in addition to quant. determination of phenols, flavonoids, and chem. mineral elements by Inductively coupled plasma-optical emission spectrometry technique (ICP-OES). Practical applications : UHPLC/MS profiling resulted in the tentative identification of 14 compounds including fatty acids, flavones, flavonoids and sesquiterpenes. ICP-OES technique showed that Algerian N. procumben represents a potential source for essential macronutrient like Na, Fe, Ca, and K, it is also a rich source of phenolic compounds evidenced by its high total phenol content (56.23 mg GAE/g extract) and high total flavonoid content (30.10 mg RE/g extract). It also revealed a significant antioxidant potential in DPPH, CAT, and ABTS assays with EC50 equals to 75.84 mg TE/g extract, 136.55 mg eq. AG/g and 92.06 mg TE/g extract, resp., with no cytotoxic effect on hepatic and colon cancer cells revealing its relative safety. Thus, it can be concluded that N. procumbens L., acts as a promising source of antioxidants owing to its richness with phenolic compounds

Journal of Food Processing and Preservation published new progress about 30931-67-0. 30931-67-0 belongs to thiazole, auxiliary class Salt,Hydrazine,Amine,Benzothiazole, name is Ammonium 2,2′-(hydrazine-1,2-diylidene)bis(3-ethyl-2,3-dihydrobenzo[d]thiazole-6-sulfonate), and the molecular formula is C18H24N6O6S4, Category: thiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

McCarren, Patrick published the artcileAvoidance of the Ames test liability for aryl-amines via computation, Quality Control of 31784-71-1, the publication is Bioorganic & Medicinal Chemistry (2011), 19(10), 3173-3182, database is CAplus and MEDLINE.

Aryl-amines are commonly used synthons in modern drug discovery, however a minority of these chem. templates have the potential to cause toxicity through mutagenicity. The toxicity mostly arises through a series of metabolic steps leading to a reactive electrophilic nitrenium cation intermediate that reacts with DNA nucleotides causing mutation. Highly detailed in silico calculations of the energetics of chem. reactions involved in the metabolic formation of nitrenium cations have been performed. This allowed a critical assessment of the accuracy and reliability of using a theor. formation energy of the DNA-reactive nitrenium intermediate to correlate with the Ames test response. This study contains the largest data set reported to date, and presents the in silico calculations vs. the in vitro Ames response data in the form of beanplots commonly used in statistical anal. A comparison of this quantum mech. approach to QSAR and knowledge-based methods is also reported, as well as the calculated formation energies of nitrenium ions for thousands of com. available aryl-amines generated as a watch-list for medicinal chemists in their synthetic optimization strategies.

Bioorganic & Medicinal Chemistry published new progress about 31784-71-1. 31784-71-1 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Chloride,Amine, name is 5-Chlorothiazolo[5,4-b]pyridin-2-amine, and the molecular formula is C6H4ClN3S, Quality Control of 31784-71-1.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Sun, Qing published the artcileFacile preparation of dihydro-1,4-benzothiazine derivatives via oxidative ring-expansion of 2-aminobenzothiazoles with olefins, COA of Formula: C7H5ClN2S, the publication is Chemical Communications (Cambridge, United Kingdom) (2022), 58(13), 2216-2219, database is CAplus and MEDLINE.

A concise and efficient approach to prepare dihydro-1,4-benzothiazine derivatives I (R¹ = H, 7-Br, 5,7-difluoro, 5-OMe, etc.; R² = Ph, naphthalen-2-yl, ethyloxidanyl, etc.; R³ = H, Me, Ph), Et 9-cyano-3,3a,9,9a-tetrahydro-2H-benzo[b]furo[2,3-e][1,4]thiazine-6-carboxylate and Et 10-cyano-4b,10,10a,11-tetrahydrobenzo[b]indeno[2,1-e][1,4]thiazine-7-carboxylate is described via oxidative ring-expansion of 2-aminobenzothiazoles II with olefins R²CH=CHR³ under metal-free conditions. This protocol is applicable for a wide range of readily accessible 2-aminobenzothiazoles II and olefins with moderate-to-good yields. The [4+2] heteroannulation between the intermediacy of oxidative ring-opening of 2-aminobenzothiazoles II and olefins is suggested to rationalize the formation of the product.

Chemical Communications (Cambridge, United Kingdom) published new progress about 95-24-9. 95-24-9 belongs to thiazole, auxiliary class Organic Pigment, name is 6-Chlorobenzothiazol-2-ylamine, and the molecular formula is C8H7ClO3, COA of Formula: C7H5ClN2S.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica